Triethylamine → HCID 178513788, compound

Participants

Reaction Steps

1-((Z)-2-Amino-1,2-dicyanovinyl)-3-(trans-4-hydroxycyclohexyl)urea. Trans-4-hydroxycyclohexane carboxylic acid (3.0 g, 20.80 mmol), triethylamine (2.10 g, 20.80 mmol) and diphenylphosphorylazide (5.72 g, 20.80 mmol) were combined in toluene and stirred at room temperature. The reaction was monitored via thin layer chromatography (50% ethyl acetate in hexanes, KMnO4 stain). After 30 min, the solution was condensed under reduced pressure and the oil diluted with acetonitrile (30 mL) followed by the addition of diaminomaleonitrile (2.24 g, 21.84 mmol). The solution was heated to 65° C. for 16 h. The resultant heterogeneous mixture was triturated with water. The resultant precipitate was filtered and dried under vacuum to afford the title compound (1.60 g, 31%). MS (ESI) m/z 250.1[M+1]+.

Provenance & Evidence